Why in Nucleophilic addition-elimination reactions,does the C=O bond break when the nucleophile is added and not theC-CL bond ?

1 Answer
anor277
Nov 21, 2016

I take it you refer to nucleophilic attack on an "acyl halide"?

Explanation:

"Reaction: " Nu^(-) + Cl(O=)CRrarr(Nu)(""^(-)O)(Cl)CRrarr Nu(O=)CR +Cl^-

The carbonyl is presumed to stabilize the negative charge of the nucleophile, presumably by resonance. The ipso carbon is thus 4-coordinate, and we could trap such an intermediate by quenching with, say, Me_3SiCl to give (Nu)(Me_3SiO)(Cl)CR.

Does this address your query?

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